Benzoyl Peroxide → 5-(Bromomethyl)-2-chloro-3-fluoropyridine

HRID 1519011Notes

Reaction equation

HRID 1519011 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1.[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:10][CH2:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([Cl:1])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 135413652-Chloro-3-fluoro-5-methylpyridine

Product 1

HCID 592970785-(Bromomethyl)-2-chloro-3-fluoropyridineYield 51%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-chloro-3-fluoro-5-methylpyridine in an amount of 4.00 g (27.6 mmol) was dissolved in 80 mL of carbon tetrachloride, following which 7.37 g (41.4 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added and the mixture was refluxed overnight under heating. Following reaction completion, the reaction mixture was returned to room temperature, concentrated under reduced pressure, and purified by silica gel column chromatography (hexane/ethyl acetate=19:1), giving 3.06 g of 5-(bromomethyl)-2-chloro-3-fluoropyridine (yield, 51%).

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed overnight
  3. temperatureunder heating
  4. customreaction completion
  5. customwas returned to room temperature
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel column chromatography (hexane/ethyl acetate=19:1)

Sources & evidence

ORD record
ord-674710ec3a4f4c3b808d9de8c33f3999
Source dataset
uspto-grants-2015_07
Patent number
US09073866B2

Reaction notes

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